Epichlorohydrin → 1-(2-Methyl-4-hydroxynaphthoxy)-3-[4-(2-hydroxyphenyl)-1-piperazinyl]propan-2-ol hydrochloride

HRID 277636Notes

Reaction equation

HRID 277636 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](O)=[C:11]([CH3:20])[CH:10]=1)C1C=CC=CC=1.C(=O)([O-])[O-:22].[K+].[K+].[Cl:27][CH2:28][CH:29]1[CH2:31][O:30]1.Cl.[OH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>C(N(CC)CC)C>[ClH:27].[CH3:20][C:11]1[CH:10]=[C:9]([OH:8])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[O:30][CH2:31][CH:29]([OH:22])[CH2:28][N:43]1[CH2:44][CH2:45][N:40]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[OH:33])[CH2:41][CH2:42]1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 120516544-Benzyloxy-2-methylnaphtholHCID 226254062-(Piperazin-1-yl)phenol hydrochloride

Product 1

HCID 226254141-(2-Methyl-4-hydroxynaphthoxy)-3-[4-(2-hydroxyphenyl)-1-piperazinyl]propan-2-ol hydrochlorideYield 39.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Using 3.7 g of 4-benzyloxy-2-methylnaphthol, 1.4 g of anhydrous potassium carbonate, 5.0 g of chloromethyloxirane, 2.3 g of 1-(2-hydroxyphenyl)piperazine hydrochloride and 1.2 g of triethylamine, reaction was carried out as in Examples 1-A and 2. The thus obtained crystals were recrystallized from ethanol-isopropyl ether to give 1.8 g of crystals, m.p. 267-269° C. (decomp.).

Workup

  1. customThe thus obtained crystals were recrystallized from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-849ae2fd4a8b4d4db01f8612b7fef821
Source dataset
uspto-grants-2002_03
Patent number
US06358515B2

Reaction notes

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